(CNN) -- If those coveted 20-something readers can't identify with Hugh Hefner, maybe they will with "The Simpsons."

Marge Simpson will appear in the November issue of Playboy as the magazine's first cartoon cover model.

Like nearly everything printed on paper these days, Playboy magazine has been facing tough times. Advertising pages have dropped 31 percent over the last year, newsstand sales have dried up by 25 percent, and its circulation has dipped to 2.4 million, according to publishing insider Media Industry Newsletter.

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Part commemoration of "The Simpsons'" 20th anniversary, part nod to the golden days of Playboy, what has become known as "The Marge Simpson Cover" has drummed up more attention for Playboy than the premiere of the original "Girls Next Door." But it remains to be seen whether the animated move can open the wallets of a younger generation.

"The shock value always does Playboy very good," said Media Industry Newsletter online editor-in-chief Steve Cohn. "This is a novelty one, but it's no different than a celebrity. In a sense, Marge has something in common with a woman who's never done it before, someone like Nancy Sinatra."

But it's not exactly shock value Playboy is going for -- more like "hip, cool" and the kind of magazine a 25-year-old would read. Maxim, a "lad mag" with an average reader of 29, also ran a cover of Marge Simpson in 2004, depicting the d'oh-eyed beauty in a sheer dress on all fours, scrubbing the floor.

"We knew Marge's pictorial would appeal to a large demographic," said Playboy editorial director Jimmy Jellinek. "This cover and pictorial is just another example of how we're evolving our editorial content to continue to reach men in their 20s, and also maintain the elements of the magazine that have attracted readers for more than 50 years."

The three-page pictorial, featuring a scantily-clad Marge in cartoon lingerie, was "obviously tongue-in-cheek," new Playboy CEO Scott Flanders told the Chicago Sun-Times. "It had never been done, and we thought it would be hip, cool and unusual."

Playboy's use of "hip" isn't the only thing retro-cool -- the cover is a clear nod to the empire's peak in the 1970s. Marge's now infamous image, itself considered to be groundbreaking as the first cartoon character to land a Playboy cover, was inspired by another bunny-eared milestone: The October 1971 issue featured Darine Stern, the first black woman to pose on a Playboy cover.

Darine Stern's picture on the October 1971 cover served as the inspiration for Playboy's November 2009 cover.

"We decided to re-create [it] because it's one of our most iconic covers," Jellinek said, "and because Marge's sexy blue beehive immediately made us think of Darine Stern, whose beautiful, voluminous hairdo was front and center on the October 1971 cover."

For Hefner, "Marge Simpson is the quintessential girl next door who stole our hearts 20 years ago and has held them captive ever since. We were delighted to learn she wanted to grace the pages of our magazine. Her pictorial is truly stunning," he told CNN.

This move comes on the heels of a disappointing first half of 2009, during which Playboy lost some attention from the demographic it does have -- the average reader is a 35-year-old male. The magazine came in 200,000 short of its 2.6 million rate base -- the minimum circulation a magazine promises to advertisers -- according to BusinessWeek.

Playboy's lackluster showing as of late can be attributed to two things, Cohn said. One, the audience transferred some of their desire for tastefully disrobed women to the Web. Second, Hugh Hefner got old.

"The reason for their audience shift can be seen in Hugh Hefner. I went to college in the '70s and Hefner was in his 40s back then. He was the symbol for what kind of guy I wanted to be," Cohn said. "Now he's in his 80s -- it's hard to identify with someone like that. That's a problem for Playboy."

But, Jellinek said, "Playboy is a state of mind and a way of being, not a pre-prescribed age. We knew this was something that all of our readers would enjoy, because the show has been on for 20 years and it resonates with adults of all ages."